Winter in Toronto is such a magical and beautiful experience, but nothing compares to the charming atmosphere of small towns in Ontario. The historic buildings, quaint boutiques, and vibrant foliage make this special season one of the best times to visit, not to mention all of the gorgeous hikes you can do while you’re there.

Here are 7 of the most charming small towns to visit during winter in Ontario.

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Ancaster & Dundas


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Dating back to the late 1700s, Ancaster is one of the oldest towns in all of Ontario.

Its historic charm has been preserved through dozens of heritage buildings and a charming main strip, where you’ll find all kinds of spots to dine including the dreamy Ancaster Mill.

Also nearby is the beautiful town of Dundas, a beautiful town in the Dundas Valley that’s lined with shops, restaurants, and cafes.

Take a drive through the nearby countryside and be sure to stop at the nearby frozen waterfalls and conservation areas, including Tiffany Falls, Webster Falls, and Christie Lake.


This small town in Ontario was named the “prettiest” in Canada by none other than the late Queen Elizabeth II, so you know you’re in for something special.

Goderich, Ontario is a small coastal town situated on bluffs with a gorgeous view of Lake Huron. The town is known for its almost turquoise-blue beaches (three in fact) and a very charming historic downtown.

In the winter, it offers some incredible views! This is the perfect day trip destination.

It’s also home to a very picturesque boardwalk.


Dreaming of wine country? Look no further than Niagara-on-the-Lake. The lovely waterfront town is filled with things to do and the surrounding heritage homes only add to its charm.

Between the luxurious 124 on Queen hotel and spa, Prince of Wales, and Harbour House Hotel, you’ll be spoiled for choice with dreamy accommodations.

And while you’re there, you can stop at one of the many nearby vineyards for a tasting. Plus, the proximity to Niagara Falls and the Niagara Botanical Gardens makes this town an easy choice.



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What better place to spend a winter weekend than in Ontario’s “most beautiful village?” When it comes to scenic views and historic charm, especially in the winter, Elora does not disappoint.

You’ll want to take a peek inside of the adorable boutiques that line the streets of this quaint destination and if you’re in the mood to spoil yourself, you can visit the iconic Elora Mill & Spa for some relaxation.


Often called one of the “prettiest towns in Ontario,” this spot is more of a hike from the Toronto area than the ones previously mentioned, but it’s totally worth the drive.

The blend of historic 19th-century architecture and the serene parks and waterways give Perth a postcard-like atmosphere — the town has worked hard to preserve its heritage feel over the years.

There are several scenic bridges you can cross to enjoy the view too.

All of these features are on display at the town’s famous Stewart Park, which is home to the Stewart Park Rainbow Bridge, rustic restored mill, and towering old trees.


Known as Ontario’s “friendly town,” you can count on a big dose of winter vibes in charming and picturesque Almonte.

The town’s historic Mill Street is so vibrant this time of year.

The scenic mill town on the Mississippi River near Ottawa is full of shops, restaurants, and elegant inns, making it the perfect weekend destination.